Hydrochloric Acid → HCID 59272921, compound

HRID 1406583Notes

Reaction equation

HRID 1406583 reaction equation
[O:1]1[C:6]2[CH:7]=[C:8]([C:11](=[O:22])[C@@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])[CH:9]=[CH:10][C:5]=2[CH2:4][O:3][CH2:2]1.C(O[Al](OC(C)C)OC(C)C)(C)C.CC(O)C.Cl>C1(C)C=CC=CC=1>[O:1]1[C:6]2[CH:7]=[C:8]([C@@H:11]([OH:22])[C@@H:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH3:13])[CH:9]=[CH:10][C:5]=2[CH2:4][O:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 16685055Aluminum tri-iso-propoxideHCID 59272924HCID 59272924, compound

Product 1

HCID 59272921HCID 59272921, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture (S)-tert-butyl 1-(4H-benzo[d][1,3]dioxin-7-yl)-1-oxopropan-2-ylcarbamate (I3c) (680 mg, 2.21 mmol), triisopropoxyaluminum (140 mg, 0.69 mmol) and propan-2-ol (3 mL, 38.9 mmol) in toluene (3 mL) was stirred at +65° C. for 15 hours. The reaction mixture was allowed to cool down and poured into 1M HCl (50 mL) and extracted with EtOAc (2×50 mL). The organic phase was washed with water, brine, dried over MgSO4, filtered and solvents removed by evaporation to afford a crude product as a colourless solid. The crude product was first purified by Flash chromatography, (solvent A=Heptane, solvent B=EtOAc+10% MeOH). An gradient of 10% B to 50% B in A was used. The obtained product was crystallised from DCM/Heptane to afford the subtitle compound colourless needles. Yield 414 mg (60%)

Workup

  1. temperatureto cool down
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customsolvents removed by evaporation
  7. customto afford a crude product as a colourless solid
  8. customThe crude product was first purified by Flash chromatography, (solvent A=Heptane, solvent B=EtOAc+10% MeOH)
  9. customThe obtained product was crystallised from DCM/Heptane

Sources & evidence

ORD record
ord-5fe16d7fbf0b4905986f6334749c99f2
Source dataset
uspto-grants-2014_12
Patent number
US08916600B2

Reaction notes

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